Docking Imines and Amines Against Tubulin Using Autodock Vina

Researchers: Andrew SID Lang, Lori Fielding, Jesse Patsolic, and Matthew Wilson

Objective

To dock library 10 (570 imines and 570 amines) UClib010output against tubulin using vina (version 1.1.1) autodock vina on ORU's cluster.

Procedure

The SMILES of the imine and the reduced imine columns from the UClib010output spreadsheet were saved as plaintext and saved as a .smi file. This file was used as input to the molconvert program which is part of the JChem and Marvin suites by ChemAxon. The output (UClib010outputPDB.zip) of the molconvert program yields one .pdb file per SMILE. [Describe the code used for molconvert. JP]

The .pbd files were then converted into .pdbqt files which are required for autodock vina. [What program did you use to convert the files? -JP]

The 1140 .pdbqt files were then run through autodock vina on the ORU cluster computer in about 9 hours. The output from autodock vina was processed into a table giving the best energies for each ligand. [Add vina code. JP]

The top ten energies for the Imines are given in the following table. The full table is given here: ImineEnergies20120218.csv.

Ligand
Energy
SMILES
Imine46
-8.7
C(c2cc3c(c1c2cccc1)cccc3)=Nc1cc(Cl)ccc1
Imine8
-8.7
C(c2cc3c(c1c2cccc1)cccc3)=Nc1ccccc1Cl
Imine236
-8.5
C(c2cc3c(c1c2cccc1)cccc3)=NC1CCCCC1
Imine122
-8.4
C(c2cc3c(c1c2cccc1)cccc3)=Nc1ccccc1
Imine160
-8.3
C(c2cc3c(c1c2cccc1)cccc3)=NCc1ccccc1
Imine21
-8.2
C(c1cc(C(F)(F)(F))cc(C(F)(F)(F))c1)=Nc1ccccc1Cl
Imine84
-8.1
C(c2cc3c(c1c2cccc1)cccc3)=NCc1oc(cc1)C
Imine59
-8
C(c1cc(C(F)(F)(F))cc(C(F)(F)(F))c1)=Nc1cc(Cl)ccc1
Imine63
-8
C(C2=CC=C(OC)C1=CC=C(OC)C=C12)=Nc1cc(Cl)ccc1
Imine274
-7.9
C(c2cc3c(c1c2cccc1)cccc3)=NCc1ccco1

The top Imine is depicted below.

C(c2cc3c(c1c2cccc1)cccc3)=Nc1cc(Cl)ccc1.gif

The top ten energies for the ReducedImines are given in the following table. The full table is given here: ReducedImineEnergies20120218.csv.

Ligand
Energy
SMILES
ReducedImine8
-8.5
C(c2cc3c(c1c2cccc1)cccc3)Nc1ccccc1Cl
ReducedImine46
-8.3
C(c2cc3c(c1c2cccc1)cccc3)Nc1cc(Cl)ccc1
ReducedImine122
-8.2
C(c2cc3c(c1c2cccc1)cccc3)Nc1ccccc1
ReducedImine236
-8
C(c2cc3c(c1c2cccc1)cccc3)NC1CCCCC1
ReducedImine45
-8
C(C(c1ccccc1)c2ccccc2)Nc1cc(Cl)ccc1
ReducedImine7
-7.9
C(C(c1ccccc1)c2ccccc2)Nc1ccccc1Cl
ReducedImine59
-7.8
C(c1cc(C(F)(F)(F))cc(C(F)(F)(F))c1)Nc1cc(Cl)ccc1
ReducedImine63
-7.8
C(C2=CC=C(OC)C1=CC=C(OC)C=C12)Nc1cc(Cl)ccc1
ReducedImine121
-7.7
C(C(c1ccccc1)c2ccccc2)Nc1ccccc1
ReducedImine56
-7.7
C(c1ccc2ccccc2(c1))Nc1cc(Cl)ccc1

The top Reduced Imine is depicted below.

20120222C(c2cc3c(c1c2cccc1)cccc3)Nc1ccccc1Cl.gif